KR870007896A - Method for preparing 2-cyanobenzimidazole derivative - Google Patents

Abstract

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Description

Method for preparing 2-cyanobenzimidazole derivative

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Claims (26)

2-cyanobenzimidazole derivative of the following general formula (I). (Wherein R ″ represents a dialkylamino group having from 2 to 4 carbon atoms) The 2-cyanobenzimidazole derivative according to claim 1, wherein R ″ represents a dimethylamino group. A bactericidal composition comprising the compound according to claim 1 as an active substance. 4. A bactericidal composition according to claim 3, which contains an inert carrier and / or surface active agent which can be used for agriculture in addition to the active substance. The composition of claim 4 containing 0.5-95% by weight of active substance and 0-20% by weight of surfactant. 2-cyano-4-bromo-6-trifluoromethylbenzimidazole of Formula (VI) or an optionally substituted alkali metal or alkaline earth metal or ammonium salt thereof is reacted with a halide of Formula (VII) Method for producing a compound of the general formula (I) characterized in that the. (Wherein R ″ represents a dialkyl amino group having from 2 to 4 carbon atoms, and X represents a halogen atom, preferably a chlorine atom) The process of claim 6 wherein the reaction between 2-cyano-4-brobo-6-trifluoromethane benzimidazole and halide is carried out in a polar aprotic solvent in the presence of an acidic solution. 8. A process according to claim 7, wherein the reaction between the optionally substituted alkali or alkaline earth metal or ammonium salt of benzimidazole and the halide is carried out in a polar aprotic solvent. Use of the derivative according to claim 1 as a fungicide. Use of a derivative according to claim 9 as an antibacterial fungicide of dicot plants, tobacco, grapes and cucumber plants. A crop processing method for plant pathogens, characterized in that the crop is treated with an effective amount of the derivative or composition formed according to any one of claims 1 to 5. Process according to claim 11, wherein the derivative according to claim 1 or 2 is used from 2 g / ha to 250 g / ha, preferably from 4 g / ha to 220 g / ha. A combination of at least one derivative of the general formula (I) and at least one fungicide of the group (II) of the following kind. (Wherein R ″ represents a dialkylamino group having from 2 to 4 carbon atoms) Group II fungicides 1. Chloride or nitride derivatives of benzene, such as kintogen or chlorothalonil. 2. Cycloimides and dicarboximide derivatives such as captans, flepts, captapol, iprodione, procmidone, vinclozoline, fluoromides, clozolinates and metomeclones. 3.Contains one or more hetero rings, such as quinoline (ethoxylated), morpholine (dodemorph, tridemorph, fenpropormorph), piperidine (phenproridine) and piperazine (triporin) derivative. 4.Dithiocarbamic acid derivatives such as maneb, mancozeb, tiram, metiram or geneb or propineb. 5.Phenol derivatives such as dinocap or vinacryl. 6.Dithiane and quinone derivatives such as chloranyl. Carbamic acid and benzimidazole derivatives such as 7, carbendazim, benoyl, thiophanate-methyl, thibendazole and fuberidazole. 8. Sulfur derivatives or sulfur and phenaminosulf, such as dazomet or ethridazole. 9.Diazines or triazines, such as chinomethionate penarimol, anilazin, noarimol, burimat, ethylimole, pyrazophos and diclomezin. 10.Sulfamides such as diclofloanide and tolylufluoride. 11.Guanidine, such as douganidine. 12.Diniconazole or other known triazoles, propiconazoles, triadimapones, triadimenols, diclobutrazole, bitteranol, fenconazole, hexaconazole, flusilazole, microclobutanyl, Triazoles such as SAN619F (acidose), ethyltrianol, fluorotrimazole and flutriafol, for example those described in British Patent No. 2,046,260, and 2- (2,4- described in European Patent Application No. 0,151,084. Triazoles such as dichloro-1-phenyl) -2-methyl (1,2,4-triazol-1-yl) -5-trifluoroethoxy tetrahydrofuran or salts thereof. 13.Imidazoles and triflumisols such as prochloraz or imazalyl. 14.Organic or inorganic copper derivatives such as copper or cuproic acid. 15. Organic tin compounds, such as pentine acetate. 16.Aniazine. 17. Amine phosphite as described in Belgian Patent No. 890,114. 18. Pyridine derivatives such as butiobate and pyriphenox. 19. 2-aminopyridine derivatives such as fluazinam. 20. isoxazoles and isoxazolone derivatives such as hismexazole and dragoxolone, and 21.Resistant to dietofencarb (isopropyl-3,4-diethoxyphenyl carbamate), phenylcarbamate derivatives such as methyl N- (3,5-dichlorophenyl) carbamate, and benzimidazole Other products active against phosphorus fungi (eg Botrytis cinerea). The composition of claim 13, wherein group (II) comprises chlorotalonyl, iprodione, pentyneacetate, dinocap, maneb, mancozeb, geneb, captan, captapol, follort, procmidone, copper and copperoxy Combinations consisting of copper derivatives such as chloride or copper quinolate. The combination according to claim 13 or 14, which further contains at least one type of fungicide selected from the following. a) phosphoric acid or its alkali metal salt or phosphoric acid derivative, preferably a derivative of the general formula (II) (Wherein R 'is a hydrogen atom or an alkyl group having an alkali metal atom or a 2-4 carbon atom, M is a hydrogen atom or an alkali metal or an alkaline earth metal or an aluminum atom; n' is 1 to 3 corresponding to the valence of M) Preferably, when R 'is a hydrogen atom or an alkali metal atom, M is an alkali metal atom and n' = 1), preferably, the derivative is a metal alkyl phosphite, preferably porcetyl- Al or an alkali metal derivative of phosphoric acid or phosphoric acid itself. b) acetamides described in US Pat. No. 3,957,847, preferably compounds of the general formula (III) (Wherein R ₁ and R ₂ are the same or different and represent a C _{1 to} C ₁₃ alkyl group, preferably a C ₁ to C ₄ alkyl group), preferably simoxanyl (R ₁ = CH ₃ , R ₂ = C ₂ H ₅ ), c) the acylanilides described in Belgium patents 827,671 and 827,419 or European patent 0,026,873, preferably 1) Compound of the following general formula (IV) Wherein R ₇ and R ₃ are the same or different and represent a hydrogen atom or a C ₁ -C ₄ alkyl group, preferably methyl, or a C ₁ -C ₄ alkoxy group, advantageously R ₃ = R ₄ = methyl R ₅ is a group —CH ₂ —R ₆ (wherein R ₆ is a C ₁ to C ₄ alkoxy group, preferably a methoxy, aryl group, preferably phenyl, or a halogen atom, preferably chlorine), R ₅ is a C ₃ to C ₆ cycloalkyl group, preferably cyclopropane, or C ₅ or C ₆ containing 1 or 2 hetero atoms, preferably C ₅ heterocyclic group, preferably 2-furyl, 5- Isoxazolyl or 3-oxazolyl, R ₇ is hydrogen or a halogen atom or a C ₂ -C ₄ alkyl group, preferably methyl], advantageously metallaxyl, furlaxyl or benalyl, R ₃ = R ₄ = CH ₃ , R ₇ = H, R ₅ = 5-isoxazolyl (LAB 149,202F), or 2) a compound of formula (V) Wherein R ₃ , R ₄ , R ₅ , R ₆ and R ₇ are as defined in formula (IV), and R ₈ is 3-oxazolidinononyl or 3-butyrolactolyl ring or 3- Thiobutyrolactonyl or 3-thiooxazolidinonyl), advantageously oxadixyl, ciprofuram, opurace, R ₃ = R ₄ = methyl, R ₇ = H, R ₅ = -CH ₂ OCH CGA68099 (RE 26,745) which is ₃ , R ₈ = 3-butyrol lactonyl, R ₃ = R ₄ = CH ₃ , R ₇ = H, R ₅ = -CH ₂ OCH ₃ , R ₈ = 3-thiobutyrol lacto Mn 2,279 which is RE 26,940 and R ₃ = R ₄ = CH ₃ , R ₅ = -CH ₂ OCH ₃ , R ₇ = 3-Cl, R ₈ = 3-oxazolidinononyl. The combination according to any one of claims 13 to 15, wherein the weight ratio of the compound of group (I) to the compound of group (II) is between 1: 10,000 and 100, preferably between 1: 1,000 and 10. The combination according to any one of claims 13 to 16, in particular for continuing to be used separately or for a period of time, in particular for sterilizing the crop with an anti-bacterial fungicide. Use of the combination according to any one of claims 13 to 16 as an anti-bacterial fungicide of dicot plants, tobacco, grapes and cucumber plants. A bactericidal, patented anti-bacterial composition comprising the combination according to any one of claims 13 to 17 and at least one inert carrier acceptable to agriculture. 20. A composition according to claim 19 containing from 0.5 to 95% of active substance. A method for inhibiting fungal diseases, in particular, fungal diseases of plants, characterized in that the plants are treated with a combination according to any one of claims 13 to 17 or an effective amount of the composition according to any one of claims 19 to 20. The process according to claim 21, wherein the derivative according to claim 1 or the composition produced from any one of claims 3 to 5 is used at a concentration of 2 to 250 g / ha for a derivative of formula (I) and 100 for a compound of group (II) Process at a rate of -3,000 g / ha. A process for the preparation of a combination according to any one of claims 13 to 17, characterized in that the compound of group (I) is mixed with the compound of group (II). The compound of the following general formula (VI) or (iii) or an optionally substituted alkali metal or alkaline earth metal or ammonium salt. Aniline derivatives of the following general formula (VII) or (iii) or salts with strong acids, or 2-bromo-4-trifluoro methyl-6-nitroaniline 26. The compound of claim 25, wherein the strong acid and salt are 1,2-diamino-3-bromo-5-trifluoromethyl benzene monohydrocloroid. ※ Note: The disclosure is based on the initial application.